| Identification | More | [Name]
4-Methylbenzenesulfonhydrazide | [CAS]
1576-35-8 | [Synonyms]
4-METHYL-1-BENZENESULFONYL HYDRAZIDE
4-Methylbenzenesulfonhydrazide
4-METHYLBENZENESULFONYL HYDRAZIDE
4-TOLUENESULFONIC ACID HYDRAZIDE
4-TOLUENESULFONOHYDRAZIDE
4-TOLUENESULFONYL HYDRAZIDE
LABOTEST-BB LT00071719
P-TOLUENESULFONHYDRAZIDE
P-TOLUENESULFONIC ACID HYDRAZIDE
P-TOLUENESULFONYL HYDRAZIDE
P-TOLUENESULFONYLHYDRAZINE
P-TOLUENESULPHONYL HYDRAZIDE
P-TOLYL HYDRAZIDE
P-TOLYLSULFONYLHYDRAZINE
SPECS AC-907/25014186
TOLUENE-4-SULFONIC ACID HYDRAZIDE
TOLUENE-4-SULFONOHYDRAZIDE
TOLUENE-4-SULPHONHYDRAZIDE
toluene-4-sulphonohydrazide
TOSYLHYDRAZIDE | [EINECS(EC#)]
216-407-3 | [Molecular Formula]
C7H10N2O2S | [MDL Number]
MFCD00007588 | [Molecular Weight]
186.23 | [MOL File]
1576-35-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [Melting point ]
103-108 °C(lit.)
| [Boiling point ]
340.5±35.0 °C(Predicted) | [density ]
1.42g/cm3 | [vapor pressure ]
0Pa at 20℃ | [refractive index ]
1.5400 (estimate) | [Fp ]
60°C | [storage temp. ]
Flammables area | [solubility ]
5g/l | [form ]
Powder | [pka]
9.39±0.10(Predicted) | [color ]
White or off-white to slightly grayish | [Water Solubility ]
5 g/L (15 ºC) | [Sensitive ]
Moisture Sensitive | [Detection Methods]
HPLC,NMR,MS | [BRN ]
610130 | [Stability:]
Light Sensitive | [InChIKey]
ICGLPKIVTVWCFT-UHFFFAOYSA-N | [LogP]
0.55 at 25℃ | [CAS DataBase Reference]
1576-35-8(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
1576-35-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xn | [Risk Statements ]
R11:Highly Flammable.
R22:Harmful if swallowed.
R44:Risk of explosion if heated under confinement. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 3226 4.1
| [WGK Germany ]
3
| [RTECS ]
MW0210000
| [TSCA ]
Yes | [HazardClass ]
4.1 | [PackingGroup ]
II | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white powder | [Application]
p-Toluenesulfonyl hydrazide is used as a reagent for the preparation of tosylhydrazones. It was used to prepare dipyrazolo[1,5-a:4',3'-c]pyridines and 1,2,3-selenadiazole derivatives. | [Reactions]
4-Methylbenzenesulfonhydrazide as hydrogen donor in reduction reactions: A base-mediated semihydrogenation of ynamides using 4-Methylbenzenesulfonhydrazide (p-toluenesulfonyl
hydrazide) as an inexpensive and easy-to-handle hydrogen donor provides the
thermodynamically unfavorable Z-enamides exclusively without
overhydrogenation and reduction of other functional groups. | [Flammability and Explosibility]
Notclassified | [Synthesis]
General procedure for the synthesis of p-toluenesulfonyl hydrazide from p-toluenesulfonyl chloride: general method: preparation of p-toluenesulfonyl hydrazide. A mixed solution of water (300 mL) and hydrazine hydrate (12.5 g; 0.25 mol) was cooled to about 5 °C in an ice-water bath. The reaction temperature was kept below 8 °C while a tetrahydrofuran (50 mL) solution of p-toluenesulfonyl chloride (5.54 g, 0.025 mol) was slowly added under stirring. After the addition was completed, the reaction mixture was continued to be stirred at room temperature for 30 min. Subsequently, the tetrahydrofuran was removed by distillation under reduced pressure. The white solid product was isolated by filtration and washed with cold water (3 x 15 mL). Finally, the product was dried in air overnight to give pure p-toluenesulfonyl hydrazide (4.86 g; 89% yield). | [Purification Methods]
Dissolve the hydrazide in hot MeOH (~1g/4mL), filter through Celite and precipitate the material by adding 2-2.5 volumes of distilled H2O. Dry it in air or in a vacuum. [Fiedman et al. Org Synth Coll Vol V 1055 1973, Beilstein 11 II 66.] | [References]
[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4629 - 4636
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3397 - 3407
[3] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 576 - 588
[4] Patent: CN107056871, 2017, A. Location in patent: Paragraph 0022; 0030; 0038
[5] Journal of Molecular Structure, 2017, vol. 1133, p. 80 - 89 |
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